Sulfur-Containing 1,2,3-Triazoles: Synthesis and Properties

被引：5

作者：

Peng, Lifen ^{[1
,2
]}

Chen, Jiayi ^{[1
]}

Chen, Yi ^{[3
]}

Lu, Hao ^{[2
]}

Okuda, Yasuhiro ^{[4
]}

Tang, Zilong ^{[1
]}

Orita, Akihiro ^{[4
]}

Qiu, Renhua ^{[2
]}

Yin, Shuang-Feng ^{[2
]}

机构：

[1] Hunan Univ Sci, Sch Chem & Chem Engn, Key Lab Theoret Organ Chem & Funct Mol,Minist Educ, Hunan Prov Key Lab Controllable Preparat & Funct A, Xiangtan 411201, Hunan, Peoples R China

[2] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr,Minist Educ, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Peoples R China

[3] Hunan Univ Chinese Med, Sch Med, Dept Physiol, Changsha 410208, Hunan, Peoples R China

[4] Okayama Univ Sci, Dept Appl Chem, 1-1 Ridai Cho,Kita Ku, Okayama 7000005, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 06期

基金：

日本学术振兴会;

关键词：

sulfur-containing 1,2,3-triazole; sulfanyl-1,2,3-triazole; sulfonyl-1,2,3-triazole; CuAAC; bioactivity; AZIDE-ALKYNE CYCLOADDITION; CLICK CHEMISTRY; CATALYZED CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; SULFONYL AZIDES; AQUEOUS-MEDIA; INHIBITORS; COMPLEXES; MILD;

D O I：

10.1002/ejoc.202301146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfur-containing 1,2,3-triazoles display bioactivities like antidepressant, antifungal activity, antitumor, etc. Numerous approaches have been established to form sulfur-containing 1,2,3-triazoles. 4-Sulfanyl- and 5-sulfanyl-1,2,3-triazoles were produced by metal-catalyzed azide-alkyne cycloaddition (AAC), etc. N-Sulfonyl-1,2,3-triazoles were generated via the reaction of acetylides with sulfonyl azides, CuAAC. 4-Sulfonyl-1,2,3-triazoles were produced through [3+2] cycloaddition and reaction of azide with bromovinylsulfonyl fluoride. Although 5-sulfonyl-1,2,3-triazoles were formed successfully via RuAAC, their synthetic approaches were very limited. 1-Phosphinyl-2-sulfanylethynes were suitable substances to access sulfur- and phosphorus-containing triazoles. In this review, the synthesis and properties of sulfur-containing 1,2,3-triazoles were highlighted. Initially, the properties of organosulfurs, 1,2,3-triazoles and sulfur-containing 1,2,3-triazoles were briefly introduced. After stating the general procedures to construct 1,2,3-triazole skeleton, the synthetic approaches and properties of sulfur-involved 1,2,3-triazoles were sorted and described in details. According to different kinds of sulfur-containing 1,2,3-triazoles, synthetic methods and features of 4-sulfanyl-1,2,3-triazoles, 5-sulfanyl-1,2,3-triazoles, N-sulfonyl-1,2,3-triazoles, 4-sulfonyl-1,2,3-triazoles, 5-sulfonyl-1,2,3-triazoles, sulfur- and heteroatom-containing 1,2,3-triazoles were summarized. Sulfur-containing 1,2,3-triazoles display bioactivities. Numerous approaches have been established to form sulfur-containing 1,2,3-triazoles. In this review, the synthesis and properties of sulfur-containing 1,2,3-triazoles, including 4-sulfanyl-1,2,3-triazoles, 5-sulfanyl-1,2,3-triazoles, N-sulfonyl-1,2,3-triazoles, 4-sulfonyl-1,2,3-triazoles, 5-sulfonyl-1,2,3-triazoles, sulfur- and heteroatom-containing 1,2,3-triazoles, were highlighted.image

引用

页数：21

共 140 条

[51] Identification of the Clinical Candidate (R)-(1-(4-Fluoropheny1)-6-((1methyl-1H-pyrazol-4-yl)sulfonyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinolin-4a-yl)(4-(trifluoromethyl)pyridin-2-yl)methanone (CORT125134): A Selective Glucocorticoid Receptor (GR) Antagonist [J].